77 Best Fun Questions To Ask Your Boyfriend

If you’ve been looking for some fun questions to ask your boyfriend, this list has you covered! Whether you just started dating or you’re already celebrating anniversaries, pull out this list of questions to ask a guy to get to know him better!

These questions to ask your boyfriend are funny, deep, and thought-provoking! No more small talk about the football game - my fun questions to ask a guy will send the message that you really want to know him - for good and bad!

So, on your next date, order some appetizers, and dive in!

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11 Best Fun Questions To Ask Your Boyfriend

No matter how long you’ve been dating, sometimes it can be a little hard to get a conversation started. These fun questions to ask your boyfriend are unique queries to ease any awkward silences. There is so much to learn about each other. Learn more through these fun questions that you may have never thought to ask!

Here are the 11 best fun questions to ask your boyfriend:

1. What is your most memorable family event?

Good or bad, just the one that stands out the strongest.

2. Describe a fun date that only costs $20.

Then do it!!

3. When were you the proudest of yourself?

What made it such a momentous occasion?

4. What inspires you to better yourself?

Does he feel more inspired when he makes mistakes, or when he succeeds?

5. What is your fondest childhood memory?

Maybe there are some family traditions he carries in his heart.

6. What do you do when you are bored?

Solitaire? Doodle? Nap?

7. Who is your hero?

Is it an imaginary or real person? Living or passed? Why does he want to meet them?

8. What is your goal in life?

How dedicated is he to achieving it? Commit to cheering him on!

9. What's the first thing you will buy if you won the lottery?

More lottery tickets? A mansion? A private island, built for two????

10. What is something weird that you like about people?

Is it something others do intentionally or subconsciously?

11. What’s your favorite flavor of ice cream?

Is he a rocky road kind of guy? Or maybe strawberry cheesecake! There are almost as many options as there are people!

13 Fun Questions To Ask A Guy To Get To Know Your Boyfriend

Everyone wants to be fully known and fully loved! Use these questions to ask a guy to get to know him better!

Make sure to thank him for his vulnerability, and keep his answers in confidence. You’re doing more than gathering random info here - you’re showing him your love and building trust.

Here are 13 questions to ask a guy to get to know your boyfriend:

12. What would be the theme song of your life?

Would there be one for different ages?

13. Which TV sitcom would you star in?

Maybe Parks and Recreation, or New Girl?

14. How would your friends describe you?

Would they talk about his silly antics or his feats of strength?

15. What would you like to be known for?

A specific characteristic, or a historic legacy?

16. Describe your dream date

It can be anywhere in the world, for any length of time.

17. If you were a dog, what kind of dog would you be?

Is he a lazy English bulldog or an energetic Great Dane? Maybe he is somewhere in between.

18. What was the last show you binge-watched?

How long did it take, and was it worth it?

19. What is the worst lie you've ever told your parents?

How does he feel know, and has he ever told them the truth?

20. What attracts you to people?

What pushes him away?

21. When did you fall in love with me?

Was there a magic moment, or did it happen over time? Did he tell anyone?

22. What kicks your adrenaline?

Maybe a positive trigger and a negative one.

23. What age would you want re-live?

Was there one epic year he would love to experience again? Or one that was terrible and really needs a redo?

24. Do you like cuddling?

If not, what does he like?

11 Fun and also Funny Questions To Ask Your Boyfriend

Laughing together builds intimacy, so being silly is like vitamins for your relationship. These funny questions to ask a guy are great conversation starters to even more comical conversations!

Don't be afraid to let the questions get a little ridiculous. The more creative, the better! There are no wrong answers for most of these.

Here are 11 funny questions to ask a guy:

25. What gross things do people do that bothers you?

Like letting their nails grow too long or not brushing their teeth… yuck!

26. If you dropped everything and went on a road trip, where would you go?

Find out all the details! Would he go alone? How long would he travel? Is there a time of year he would prefer?

27. Where is the craziest place you have danced?

How did people react??

28. Have you ever stolen anything before?

Did he ever go back to pay for it?

29. If you had to bury treasure where would you hide it?

Would he leave a map? Where would he put it?

30. What names were ruined for you because you knew someone terrible with that name?

Who is his “Karen?”

31. What’s the weirdest celebrity crush you’ve ever had?

Do you know anyone else with that crush?

32. What kind of ice cream describes you best?

Something sweet, smooth, and a little nutty? Pure vanilla? What flavor is he? Which would you pick?

33. If I caught you lying to me, how would you save yourself?

Would he throw himself on your mercy, or come up with a grand excuse?

34. What is the wackiest gift you have ever received or given someone?

Mine was a glass decanter shaped like a pig. Can he beat that?

35. Your worst date. Describe it.

Take notes so that you never repeat it!

11 Fun but Random Questions To Ask Your Boyfriend

Maybe you’re waiting in a long line, maybe you just want to try and connect in a new way. Try using some of these random questions to ask a guy to start some new discussions!

Here are 11 random questions to ask your boyfriend:

36. Do you think I’m a good kisser?

Maybe there are some new things he would like to try!

37. What is the first thing you noticed about me?

It’s ok if it’s physical, but a bonus if it’s not!

38. Do I match your idea of a perfect partner?

What makes up his dream girl?

39. Where is the most uncomfortable place you have ever slept?

A bus? His friend’s floor? How did he get into that situation?

40. Which is more important to you, smart or happy?

Ideally both, but which one is more of a necessity?

41. If you could only keep five possessions, what would they be?

Is he a practical person, or more sentimental?

42. Do you have a secret talent and what is it?

Find out what his party skill is!

43. What food do you wish you cook like a world-class chef?

Maybe get him some tools so he can work towards this goal!

44. What would you say is your worst trait?

Is he self-reflective enough to know?

45. What are your thoughts on pickled foods that aren’t cucumbers?

They’re good for you, but what does he think to taste wise?

46. Do you consider yourself a spender or a saver?

Does money burn through his pocket, or is he a scrooge?

9 Fun but also Interesting Questions To Ask Your Boyfriend

Chances are, your boyfriend has a complex mind. These interesting questions to ask a guy will open up his inner thoughts so that you can learn and love him in a whole new way!

Finding out more about his inner thoughts shows that you value all of who he is - not just his good looks! Break out these questions and get into the nitty-gritty!!

Here are 9 interesting questions to ask your boyfriend:

47. What could I do for you that I don't do now?

Show him you want to speak his language!

48. Where do you see yourself living when you retire?

A cabin in the mountains, or a beachfront getaway?

49. Do you believe in soul mates?

Can people have more than one?

50. How do you think you best express love?

Is he a talker, or more of a doer?

51. Is love something that scares you?

Find out his relationship history.

52. What’s your favorite non-physical quality about me?

Maye it’s your sense of humor or your great taste in questions….

53. What’s your favorite way to show affection?

Is he a gift-giver? Complimenter? Grand gesture of love.

54. If I asked you to blindly follow me, would you?

No questions asked! Ok, maybe a FEW questions.

55. If you were to give me a nickname, what would it be?

And think of what you would call him!

13 Fun but Deep Questions To Ask Your Boyfriend

These questions are fun but intimate, so make sure you’re ready for them! I mean it, these deep questions to ask your boyfriend probably aren’t first-date appropriate, ok?

But, that doesn't mean these deep questions aren't important! If you guys are getting serious, you’ll be so glad you took the time to have these conversations.

Here are 13 deep questions to ask your boyfriend:

56. Are you happy with me?

Is his happiness trending upward as your relationship goes on?

57. What are your main relationship goals?

How will he know he has met them? Are they the same as yours?

58. Have you ever been afraid of your own emotions?

Is he more nervous about positive or negative emotions?

59. Do you see yourself married someday?

Maybe he wants a big wedding, or to elope? Or maybe he pictures a life free of that commitment.

60. What are your financial goals?

Does he want to be a millionaire by 30? Give 80% of his money away? Are you on the same page about your money philosophy?

61. Do you want children?

What does he imagine his ideal future family to look like?

62. What’s Something That Not Many People Know About You?

Maybe try asking this one as “2 truths and a lie”!

63. What Are You Most Afraid Of?

Spiders? Death? Telemarketers? Maybe nothing at all!

64. Do you still have feelings for an ex?

Be ready to admit this yourself if he reciprocates!

65. What would be your best reason to break up with me?

Are there any deal breakers you should know about?

66. Do you see me in your future?

Is what you have a long term thing or just fun for now?

67. Do you believe in God?

If not, what does he believe instead? What did his faith look like growing up?

68. Have you ever committed a crime?

Try and be open minded - we all make lots of mistakes when we’re young. But, pay attention too!

9 fun sexy questions to ask your boyfriend

Do you want some fun and sexy questions to ask your boyfriend? These questions will definitely get your boyfriend in a fun and sexy mood that he'll more than likely enjoy. He'll love answering these questions just as much as you enjoy asking him them.

Here are 9 fun sexy questions to ask your boyfriend:

69. What kind of outfit would look best on me?

Figure out what he loves on you and wear it whenever you feel like being a tease.

70. Have you ever been caught in the act?

Talk about an awkward situation!

71. Do you think you’re a good kisser?

If he says yes, let him prove it to you.

72. What part of my body would you want me to tattoo?

And what would he want you to tattoo in that spot?

73. Have you ever had a dream about me?

If he did, hopefully it was an exciting dream.

74. Have you ever bought lingerie for a girl?

This question should give you an idea of what type of lingerie he's into.

75. How many girls have you been with, before me?

Be prepared to control your jealousy with this question.

76. Do you think I’m a good kisser?

If he's clever, he'll ask you to kiss him so he can give you a precise answer.

77. Would you like me to give you a massage?

Who would say no to this question?

How to Pick The Best Fun Question To Ask Your Boyfriend

Maybe you’ve read through this list, but feel even more lost than before?? No worries! This is an extensive list, meant to be spread out over many, many conversations.

I've got some basic tips to help you figure out exactly where to start with this fun list. So, read on, take some notes, and get ready to pick out a few awesome, fun questions. 

Here is how to pick the best fun questions to ask your boyfriend:

1. Take your relationship pulse

Before you even start, take some quick vitals on where your relationship is. Are you guys a new couple? Coming out of a rough patch? Starting to get serious? That information will help you choose appropriate questions for your boyfriend.

If you’re pretty new or experiencing a hard season, stick to lighter questions. Use funny questions to help ignite your spark and get you more connected. If you’re taking some next steps, use the deeper questions to make sure you’re solid and daydream together about your future.

2. Seize the moment

Pick the right questions for the right times. Have a long dinner ahead of you? Maybe pick out a few for the drive, a few for the appetizer and a few for dessert! Stuck in traffic? Break out some silly questions to ease the tension.

But, just like knowing the RIGHT time to pop some questions, be aware of the wrong times, too. Don’t get so excited about asking him some of these fun questions that it gets awkward or frustrating. If the game is on, or he just got home from work, wait ‘til later.

3. Stay neutral and stay engaged

Sometimes, you may hear an answer you weren’t expecting! While you’re allowed to feel all the things, try and stay neutral if you hear a surprising answer.

Prep yourself to be a good listener. Don’t ask a question you’re not ready for an honest answer for, and keep space open for communication. Remember, these fun questions are supposed to add fun and build love and intimacy - not break it!!

Downloadable and Printable List of Fun Questions to Ask Your Boyfriend

Here is a downloadable and printable List of fun questions to ask your boyfriend (right click the image and select Save Image As...)

More Great Ways To Talk to Guys

1. Need some step-by-step instructions? Here is exactly how to start a conversation with a guy.
2. When you’re ready to make your move, use these flirty questions to ask a guy to let him know you’re super interested.
3. Casually break out some of these personal questions to ask a guy to show your man you want to know absolutely everything about him.

In Conclusion

There is so much laughter and connection waiting for you two as you plan out which of these fun questions to ask your boyfriend! And don’t stop here - I’m sure you can think of plenty of other questions to ask a guy that will help you grow even more in love.

These fun questions to ask a guy are sure to spice things up in the best way. For a date night in, or a special evening out, choose a few questions to ask your boyfriend and watch the sparks fly!